Methyl 5-(chloromethyl)-2-furoate

Methyl 5-(chloromethyl)-2-furoate [2144-37-8] is a white to yellow crystalline solid with the melting point of 29-30 °C. ^[1]  At higher temperatures it is a clear oil with the boiling point of 114-116 °C/3 mbar. It is insoluble in water and soluble in the usual organic solvents. It darkens it color after long standing.^[2] It can be prepared by Blanc type chloromethylation of commercially available methyl furan-2-carboxylate with paraformaldehyde, zinc chloride and anhydrous hydrogen chloride.^[3] Another possibility of preparation is chlorination of hydroxymethyl derivative, which can be obtained from D-glucono-δ-lactone.^[4]

Application of Methyl 5-(chloromethyl)-2-furoate:

Methyl 5-(chloromethyl)furan-2-carboxylate is used as a versatile building block in the synthesis of various biologically relevant compounds. It was used in the synthesis conjugated hydroxamic acids as a potent  anti-tumor histone deacetylase (HDAC) inhibitors.^[5] It also served as a starting material in the synthesis of furan-2-carboxamide analogues as novel positive allosteric modulators of N-Methyl-D-aspartate receptors.^[6] It was used in the synthesis of novel guanidine-derived non-peptide gonadotropin releasing hormone receptor antagonists that may serve as useful therapeutic agents for treating hormone-dependent pathologies including hormone-dependent prostate and breast cancer.^[7]

Product categorization (Chemical groups):

Main category:

• Carboxylic acid esters / Lactones
• Halides / Halide containing compounds

Second level:

• Aromatic compounds

Third level:

• Furan derivatives

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